


Matchmaking Shenanigans

by Latenightbookworm



Category: Supernatural
Genre: Blind Date, Dean is a Little Shit, Eileen Leahy Ships Castiel/Dean Winchester, Everyone Ships Castiel/Dean Winchester, F/M, M/M, Matchmaking, Movie Night, Oblivious Castiel/Dean Winchester, Sam Winchester Ships Castiel/Dean Winchester, Trapped In A Closet, but not really, little bit of case fic, or are they...
Language: English
Status: Completed
Published: 2021-03-09
Updated: 2021-03-11
Packaged: 2021-03-15 16:02:55
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 4,398
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29935911
Author URL: https://archiveofourown.org/users/Latenightbookworm/pseuds/Latenightbookworm
Summary: Dean and Cas are so obviously in love and Sam is sick of them doing nothing about it. With Eileen's help he comes up with a foolproof plan to get them together, but Dean and Cas have their heads deeper in the sand than he could ever have expected.
Relationships: Castiel/Dean Winchester, Eileen Leahy/Sam Winchester
Comments: 21
Kudos: 68





	1. Chapter 1

**Author's Note:**

> This fic is almost complete, will be finished by the end of the week :)

Sam stared down the length of the table, the book laying open in front of him completely ignored. He had tried getting Dean’s attention a couple times about five minutes ago with no luck and now he had resigned himself to timing how long his brother and Castiel would be staring at each other this time. He wasn’t even sure they knew he was in the room. At this point he was starting to get a little uncomfortable. He’d tell them to get a room, but Dean would just get all pissy and defensive and Castiel would tilt his head and look confused and Sam just did not want to deal with that right now. Of course, that’s if they heard him in the first place. 

After ten minutes of staring at his brother staring at the angel, Sam gave up on them noticing him and walked out, glancing back at the doorway. Yep, still staring. He sighed in defeat and went to track down Eileen. He found her in the kitchen contemplating the coffee machine. Sam tapped her on the shoulder and waited until she had turned around to say, “You’re thinking pretty hard at that coffee machine.”

“Trying to decide if it’s too late in the day for coffee or not. Probably is. Did you talk to Dean about that spell you found?”

Sam sighed, his mouth twisting. “Tried to, but he and Castiel were so caught up in staring at each other I’m pretty sure they had no idea I was there.”

Eileen winced understandingly. “Ooh. How long did you wait?”

“Ten minutes! And they were already there when I sat down! I mean, this is just ridiculous at this point, how can they not see it?”

“Hm. Well, maybe they’ve been stuck in this pattern for so long they just can’t see a way out,” Eileen said thoughtfully. “Maybe…”

“What?” Sam asked. “Come on, I know that face. You’ve got an idea.”

“Well… Maybe they just need a little push,” Eileen said hesitantly. “Just a little help to get them past this.”

Sam’s eyebrows shot up and he took a moment to think. He really was getting sick of the two of them and all their sexual tension that they apparently had no awareness of. Maybe if he and Eileen could get them to pull their heads out of their respective asses he wouldn’t have to deal with situations like the library anymore.

“Alright, I’m in. Anything to get them to stop staring at each other like nothing else exists.”

\-----

Sam and Eileen spent the rest of the evening brainstorming ways to get Dean and Castiel together. They started a list, writing down what they considered their best ideas. As it got later and their ideas got progressively crazier, Dean’s absence became more and more noticeable. Eventually they gave up and ate dinner without him, wondering if he and Cas were still sitting in the library staring at each other.

“I mean, they can’t be, right?” Eileen said. “It’s been hours.”

“Yeah, but Dean wouldn’t miss dinner… I don’t know,” Sam said hesitantly. “Anyway, we’ve got a pretty good list of ideas here, maybe we should go check.”

Eileen grabbed the list off the table, folding it into her pocket, and they headed over to the library. Sam peeked through the doorway before shaking his head at Eileen. Their chairs were exactly where they had been before, but no one was there. He turned back to Eileen and shrugged. 

“Guess he was tired or something.”

Eileen smirked. “Yeah, all that staring must’ve been exhausting.”

Sam laughed and they headed to their own bedroom, deciding to put their plan into action tomorrow.

\-----

**Ways to stop Castiel and Dean being idiots and just get together already  
1\. Movie night  
2\. Make them work a case together alone  
3\. Blind date  
4\. Lock them in a closet (don’t forget to angel proof it!)**


	2. Chapter 2 - Movie Night

**Summary for the Chapter:**

> Sam and Eileen set plan number one into motion. Who doesn't love movie nights?

Their first idea was perhaps a little tame, movie nights weren’t uncommon in the bunker. But Eileen figured it was best to start small, something they might not notice as a plot. They would make sure they sat together and pick something romantic or cheesy. Hopefully it would be enough and they wouldn’t have to use any of their other ideas.

That evening Dean was actually in the kitchen for dinner, Castiel trailing behind him. Sam glanced at Eileen and cleared his throat.

“Hey, I was thinking. We, uh, haven’t had a movie night in a while.”

Eileen nodded. “That sounds like a good idea, we should do that! Tonight!”

Dean glanced between them, eyebrows furrowed. “Yeah, I mean, sure. Last one was like a week ago, but you know I’m always down for a movie night. Cas?”

Castiel looked mildly irritated, but Sam figured he kind of always did and brushed it off. “I suppose. Not like I had any other plans tonight,” he responded, looking at Dean sideways.

 _Oh_ , Sam thought, fighting back a grin, _he must be nervous about sitting in a dark room next to Dean for two hours._ Little did he know that was the whole point. This might just work after all.

They finished clearing the table and Dean said he would go get a movie picked out and set up.

“Cas, you wanna come with?”

Sam panicked. What if they sat on opposite ends of the couch? Or different couches entirely? How was he supposed to come up with a reason they had to sit next to each other?

“No!” he shouted. Dean turned to look at him like he’d gone insane. He cleared his throat and started again. “No, uh, I need…” Shit, he needed to come up with something now. “Snacks! Cas, help me out with the movie snacks. And I think Eileen had a movie in mind, Dean.”

“Oooookay then. Eileen, let’s leave Mr Crazy over here to his very important snacks then.” Dean gave him one last weird look before leaving with Eileen. Sam sighed in relief and turned to Castiel, and almost immediately cringed. Cas was looking at him in confusion, peering at him with squinted eyes.

“Sam. Do you feel alright? I didn’t think ‘snacks’ were typically this important to you.”

Sam chuckled at his air quotes. “I just, uh, want to make sure everything is just right is all.”

Cas just nodded in response, still looking confused. Sam got the popcorn ready and handed a bowl to Cas, leading them down to the Dean Cave. He shared a glance with Eileen when they entered, seeing she had gotten Dean to sit on one end of a couch. He motioned for Castiel to sit next to Dean, saying they could share that bowl of popcorn. Dean looked at him oddly for that, but smiled at Cas as he sat down, definitely closer than two bros ever sat on a couch together, Sam thought sardonically. He settled in next to Eileen to watch whatever rom-com she had decided would be perfect for Dean and Castiel. Still, he found himself distracted through the whole movie, glancing over at his brother the whole time to see if it was working. Eileen didn’t seem to be doing much better. By the end of the movie, Sam was sure neither of them could have described the plot at all and, even worse, he didn’t think it had worked. Sure they looked real cozy sitting together, but no more than usual. They hadn’t talked much during, which may have been something Sam and Eileen should have considered with this plan, and they hadn’t even had one of their intense staring competitions. 

“Alright you two lovebirds, I’m headed to bed,” Dean said, standing up and stretching. “Good movie choice, Eileen, guess you can pick more often. Better than Sam’s choices ever are.” He grinned at Sam, who gave him what he knew Dean would call a classic bitchface.

Castiel stood too, nodding his good night to Sam and Eileen. Sam wasn’t sure where he went every night when they all slept, but he never saw him around the bunker. He sighed and looked at Eileen, who looked as defeated as he felt. Maybe the next plan would work better.

\-----

Dean had been suspicious ever since Sam started talking about a movie night at dinner. Hadn’t had one in a while? Who was he kidding, they had just watched _Die Hard_ four nights ago. He certainly wasn’t going to say no, but he didn’t have to make such a big deal about it. Then Sam had been so weird about Cas going with him to get the TV set up and Dean had thought maybe Sam didn’t want them making out in the Dean Cave like they usually did, but why would Sam suddenly care now? Then Eileen was so insistent on watching a rom-com, which Dean knew Sam hated and he was pretty sure wasn’t Eileen’s usual style either, but she wouldn’t say why. She was weirdly insistent on where he sat too and when Sam came in with Cas and practically pushed him into Dean’s lap he started putting the pieces together. If it weren’t for Sam keeping them separated until the movie started he’d think Sam and Eileen were trying to push them together, but- No. It couldn’t be.

“Dean,” Cas whispered. “Your brother and Eileen are acting very strange.”

So Cas had noticed too, great. “I know,” he said out of the corner of his mouth, trying to make sure they didn’t hear.

“They keep staring at us.”

“I know!”

They tried to ignore Sam and Eileen’s less-than-obvious glances and just watch the movie, but ten minutes later Cas whispered again. “Dean… I thought you said you told Sam months ago.”

“I did! I… well I thought I did anyway.”

“What does that mean?”

“Shh just watch the movie. We’ll figure it out when we go to bed.”

Cas pursed his lips and squinted at him, but turned back to the screen. They watched the rest of the movie in silence.

Once they were back in Dean’s room, Cas gave him a look. Dean knew what he wanted and thought back to his conversation with his brother. He had thought it had gone so well, but clearly he had missed something.

“Dean,” Cas said flatly.

“I know, I know. Cas, I really thought I had made it clear. Obviously I didn’t and Sam and Eileen are trying to, I don’t know, get us together or something,” Dean said, exasperated.

“Well, what did you tell him?”

“For some reason he thought we were fighting or something, I told him we weren’t. Then I told him we were doing the opposite of fighting actually,” Dean said suggestively, “and he was totally cool.” He paused. “Actually, now that I think about it, he was a little too cool. Huh.”

Cas rolled his eyes dramatically. “Well, what are we going to do now?”

Dean thought for a moment and chuckled. “I mean, it is kind of funny, if you think about it.”

Cas looked like he was holding back a smile. “Still, Dean, we have to tell him at some point.”

“Yeah, I know, but. Well. I haven’t played a good prank on Sammy in ages, let’s just let this play out a bit, see what they do.”

“Fine,” Cas said fondly. “But if this goes south I’m blaming you.”

Dean just grinned and pulled him in for a kiss.


	3. Chapter 3 - Make them work a case together alone

**Summary for the Chapter:**

> It's perfect. It can't fail. Working together alone? Guaranteed success.

So movie night hadn’t worked out how they wanted. Sam wasn’t deterred, at least they seemed to have had a good time. Even better, he had found the perfect case to send them on. A ghost in Minnesota was targeting unmarried couples and Sam knew they would have to pose as a couple to try and draw it out. He would just leave that detail out, they would figure it out once they got there.

“Dean, I’m heading to St. Louis with Eileen, she found what looks to be a werewolf. But there’s a ghost in Duluth I figured you and Cas could take care of,” Sam told him the next morning.

“Oh, the one targeting unmarried couples?”

Sam froze. “Uh, is it? Guess I missed that.”

“Really? Getting slow Sammy,” Dean said with a grin. “Wouldn’t it make more sense for you and Eileen to head to Minnesota and me and Cas can take care of your werewolf?”

“Well, uh. Eileen’s already in the car and we’ve, um, we’ve already made a couple calls so…” Sam stuttered his way through a panicked explanation. “Probably best if we follow through on those, don’t want to confuse anyone.”

“Hm. Well, what do you want me and Cas to do about this ghost? I mean, unmarried couples, just sounds like you two would be better for the job.”

Damn it, why was Dean being so pushy about this? “Dean, I’m sure you two can figure something out. Just, I don’t know, pretend to be together or something,” Sam said, trying to sound like he had just thought of it.

“Huh. Well, I’ll ask Cas, but I don’t know Sam. Ghost might be able to tell, you know? I’m sure the cops down in St. Louis would understand if we told them we got handed the case.”

Sam tried not to shout this time. “No, Dean. It’s, uh, it’s not just the cops, Eileen has some contacts down there. So, unless you want this ghost to keep killing innocent couples…”

“Alright, alright,” Dean gives in. “We’ll get it taken care of. Still, not sure how well this plan of yours will work, seems real flimsy to me.”

Sam held his breath until his brother left the room, letting out a sigh of relief. Bit more of a fight, than he had expected, but the plan was in motion and Sam was sure this one would work out better than movie night had. He hurried to the garage, eager to get on the road with Eileen.

\-----

Dean wiped the dirt of his hands and stretched his back. It had, as expected, been a simple salt and burn and had only taken him and Cas a day to track down the ghost that was killing people. They hadn’t even needed to lure it out, they had figured out who it was fairly easily and his bones were buried in a cemetery just outside of downtown. He chuckled, thinking of how hard Sam had pushed for them to take this case.

“Dean. I can drive us back if you would like,” Cas said from behind him.

“Dude, it’s way too late to be making a ten hour drive.” Dean’s face twisted at the thought. “Besides, Sam clearly thought this was going to take us some time, no need to rush out of here. There’s a mansion around here where two people got murdered and they do tours, we should check it out tomorrow.”

Cas tilted his head in Dean’s favorite way. “Do you think it’s haunted?”

“Ugh, I hope not. We’ve done enough work in this town for one trip. Just might be fun,” Dean said with a smile.

“You have a strange idea of fun, Dean.”

Dean just laughed.

They ended up spending a few days in Duluth before heading back to the bunker. Sam kept needling him for details while clearly trying to seem like he was only interested in the case, but all Dean would say was, “It was fine, it’s taken care of.” Sam looked crestfallen every time and Dean had to bite his cheek to keep from laughing.

**Notes for the Chapter:**

> The mansion Dean talks about is the Glensheen Historic Estate. I do not live in Minnesota, but it seems like the kind of thing Dean would love.


	4. Chapter 4 - Blind Date

**Summary for the Chapter:**

> This is the first chapter that I thought of when I had this idea. Dean is having way too much fun with this.

Sam could not believe the case in Duluth hadn’t worked. In fact, the way Dean clammed up every time he asked about it, it might have even backfired a little. Still, Sam and Eileen were determined and their next plan was sure to work. Neither of them could really believe they had to use it, but clearly Dean and Castiel were more oblivious than they had thought. They were going to set the two up on a blind date together, though they decided to wait a little bit to let Dean cool off from whatever had happened on that last hunt. 

Sam brought it up as casually as he could after dinner one night when he and Dean were sitting in the library sharing some whiskey. “Hey, Dean, you haven’t gone out in a while.”

Dean raised an eyebrow. “Sure I have, Cas and I just went to that new bar in Smith Center last weekend.”

“No, I meant, like, on a date. Just, um, noticed it had been a while, that’s all.” Sam kept his eyes on the table, not sure he could keep up the charade if he looked his brother in the eye.

“Really,” Dean stated dryly. “That so, Sammy.”

“Well. I may, um, I may actually know someone you might like?” Sam cringed at the way his voice rose.

“Oh, shocking.” Dean sounded on the verge of laughter. “And?”

“And I thought maybe you two could go for a drink, ok?” Sam sighed in exasperation, his brother was not making this easy on him, as usual. 

Dean was quiet for a minute, then smirked. “So… she cute?”

Sam almost winced at Dean’s assumption; was this the problem? Was Dean so far in the closet he wouldn’t allow himself to follow through on his obvious attraction to Castiel? No wonder the previous plans hadn’t worked. Sam controlled his face enough to just smile at his brother and respond, “Guess you’ll have to see for yourself.”

\-----

Meanwhile, Eileen enacted the other half of the plan with Castiel. She found him in one of the file rooms and tapped him on the shoulder. When he turned around she signed, “What are you reading?”

He shrugged, setting down the file in his hands, and signed back, “Nothing important, just looking for something to do.”

She smiled. “I know that feeling. It has been pretty quiet lately.”

Castiel nodded and she figured this was the perfect segue. “I have an idea, actually. This is probably the perfect time, too,” she signed, trying her best to look like this was a new thought. Castiel looked at her questioningly. “I have a friend who is trying to get back into dating and I think you two could really get along.”

Castiel suddenly looked awkward and Eileen was quick to reassure him. “Don’t worry, just meet for drinks and see how it goes.”

Cas still seemed unsure and couldn’t meet her eyes, but signed in response. “Ok. Might as well.”

Eileen grinned, the plan was on track and couldn’t possibly fail this time.

\-----

Sam and Eileen had sent them to the same bar they’d had their last date in, but Dean didn’t mind so much. At least he knew what was good now. They had a great time, as usual, and Dean had even gotten Cas laughing with him about the pair’s attempts at matchmaking. Time flew by, as it always did when they were together, and before Dean knew it, it had been several hours and the bartender was hinting for them to leave. 

As they climbed back into the Impala to make their way home, Cas asked if they would tell Sam and Eileen that they were together now.

“And let them think they had any hand in this?” Dean said incredulously. “Oh no. This is not the time. Not yet.”

“How will you know what the right time is?” Cas asked curiously.

“We’re getting close. They seem pretty desperate, I mean setting us up on a ‘blind date’? It’s really obvious, so if we come back and they think it still hasn’t worked... “ Dean chuckled. “That’ll drive them crazy. Oh man, I can’t wait to see Sammy’s face.”

Cas huffed a laugh and Dean’s grin widened at the sound. Cas was always so serious that it wasn’t a very common sound and Dean’s heart soared every time he got to hear it. His grin stayed firmly planted on his face the rest of the way back to the bunker, reenergized every time he glanced over at Cas in the passenger seat.

He didn’t try to hide it as they walked into the bunker from the garage and he knew as soon as he saw Sam and Eileen waiting for them in the library that they thought their master plan had worked. They both perked up, glancing at each other and unsuccessfully trying to hide their own smiles. Dean bit his cheek to keep from laughing.

“So? How was it?” Sam burst out. He looked about ready to vibrate out of his seat waiting for them to say something and Eileen was no better.

“Sammy, you will not believe it. That girl you set me up with stood me up!” Dean was having a hard time keeping himself from breaking as Sam and Eileen’s faces froze and slowly slid into incredulity. “But that’s not even the craziest part. Cas, here, was also supposed to have a date and he got stood up too. At least we didn’t end up alone at the bar, huh Cas?”

“I would have just flown home, but it was nice to spend the time with you, Dean,” Cas said with a straight face. How Cas, a notoriously bad liar, was keeping his cool, Dean wasn’t sure, but he supposed technically he hadn’t lied. 

“Thanks, buddy. Always a good time with you, too.” Dean turned back to his brother and Eileen. “Getting pretty late, I’m going to bed. Night, lovebirds!”

Sam and Eileen just stared in frozen shock as Dean and Cas walked out.


	5. Chapter 5 - Lock them in a closet

**Summary for the Chapter:**

> Last chapter! Dean and Cas finally come out of the closet ;) (so sorry for that pun, I could not resist)

Sam and Eileen sat in the library in shocked silence far longer than either of them wanted to admit. When Sam finally felt like he could say something, anything he signed, “How… How did that not work?”

Eileen looked at him, her eyes reflecting back his own confusion. “I don’t know. It was. It was so obvious.”

They fell still again for a moment. Sam sighed. “Only one idea left.”

“It was a joke though!” Eileen signed furiously. “We weren’t supposed to actually have to use it!”

“I know.” Sam looked defeated. “But what else can we do?”

“I guess.” 

They stared at each other tiredly before Sam stood. “Let’s go to bed. We can do it tomorrow.”

Eileen nodded and followed him to their room.

\-----

The next morning they woke with fresh determination. Sam was again in charge of Dean and Eileen responsible for Cas. Dean usually woke up much later than they did and they used the time to paint angel wards on the door to the small storage room they planned on using so that Cas was just as locked in as Dean. Sam still wasn’t sure what Cas did while they all slept, but somehow he always seemed to turn up when Dean finally got out of bed each day. It took until almost lunch time before they wandered into the kitchen and as soon as Dean had finished eating, Sam practically dragged him down the hall saying something about a new spell he had found in the library. Dean looked behind him at Cas as he followed his brother out with an odd expression on his face. 

Eileen waited a couple minutes before turning to Castiel, sure that Sam would be in the room gathering ingredients with Dean by then. “I think Sam actually needs your help with the spell, he must be pretty excited to have forgotten.”

Castiel gave her a small, almost amused smile as he stood. “Lead the way then.”

She walked with him down the hall and stopped at the door, waiting by where it was fully opened so he couldn’t see the wards they had painted earlier that day, and gestured him inside. Castiel walked over to Dean and Sam and Sam handed him a book. “Great, you’re here. One moment, just have to grab something.”

He walked out and as soon as he crossed the threshold, Eileen slammed the door and quickly locked it. They grinned at each other, knowing Dean and Cas were sure to figure their shit out quickly now. They stood outside the door waiting to hear what they said, Eileen watching Sam for his translation. Sam could hear them talking to each other but it was low enough he couldn’t make out what they were saying. He was pretty sure he heard Dean laugh and then there was a thud. _Oh no. Did he piss Castiel off again?_ Sam worried. Them fighting again was not what he wanted. A crash, like something had fallen and then…

“What is it?” Eileen asked, staring at Sam’s stricken face. “What are they saying?”

Sam wanted nothing more than to cover his ears and run but he was frozen in horror. “They aren’t. They aren’t talking. They’re… Oh god. Eileen. They’re…”

Eileen’s eyes grew wide. “No! They aren’t…?” She couldn’t finish the sentence.

Sam only nodded as the moans and banging noises grew louder through the door. There was another crash, louder than the first, and everything suddenly stopped. Sam cringed and waited with bated breath.

Dean’s laughter boomed through the door and Sam could even hear Castiel laughing. His horror quickly turned to confusion and then the door opened. Dean was still laughing as he and Cas walked out of the room. Sam’s confusion only grew - they were both, thankfully, still clothed. It took a full two minutes before Dean had stopped laughing enough to speak. Castiel stood next to him with the widest grin Sam had ever seen on his face. Sam and Eileen could only stare.

“Oh Sammy. Your face… It’s too perfect,” Dean chuckled, looking smug.

“What… I feel like I’m missing something,” Sam said.

“Yeah. You missed something like four months ago, man. You know, when I told you Cas and I were doing ‘the opposite of fighting’?” Dean said, looking at him pointedly. 

Sam suddenly got it. “Really?” he said incredulously. “Oh man. How did I miss that?”

“I don’t know, Sam, thought you were supposed to be the smart one,” Dean said laughingly. “Now if you’ll excuse us…” He looked over at Cas and winked. “We’re going to go have real sex now.” He grinned at Sam and Eileen’s blanched faces, grabbed Cas’ hand, and left them to clean up the mess they had made of the storeroom.


End file.
